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. 2017 Sep 6;6(6):740–754. doi: 10.1039/c7tx00223h

Table 2. Formation of covalent o-quinone-DNA adducts.

Quinone Treatment Conditions Structure of Adduct Method of Detection Reference
Estrone-2,3-dione 2-OHE1 + MnO2 + dG + acetic acid/water 2-OH-E1-6-N2-dG NMR Stack et al.72
2-OHE1 + MnO2 + dA + acetic acid/water 2-OH-E1-6-N6-dA
Estradiol-2.3-dione 2-OHE2 + MnO2 + Ade + acetic acid/water 2-OH-E2-6-N3-adenine NMR Zahid et al.71
2-OHE2 + peroxidase + Calf thymus DNA 2-OH-E2-6-N3-adenine HPLC
32P-post-labeling
Estrogen-3,4-dione 4-OHE1/E2 + MnO2 dG + acetic acid/water 4-OH-E1-1-N7-guanine NMR Stack et al.72
4-OH-E2-1-N7-guanine
Estrogen-3,4-dione 4-OHHE2/E1 + MnO2 + Ade + acetic acid/water 4-OH-E1(E2)-1-N3-adenine NMR Zahid et al.71
4-OHE2/E1 + Peroxidase + Calf thymus DNA 4-OH-E1(E2)-1-N3-adenine NMR Li et al.73
4-OHE2 or E-3,4-dione 4-OH-E1(E2)-1-N7-guanine LC-MS
ACI Rat Mammary Gland 4-OH-E2-1-N3-adenine HPLC
4-OH-E2-1-N7-guanine 32P-post-labeling
4-OHEN 4-OHEN in MetOH 2-N1,3-(N2-dG)-1,3-Dihydroxy-5,7,9(10)-estratriene-4,17-dione. 1H-NMR, 13C-NMR and LC/MS Shen et al.18
dG, dA or dC 1-N6,3-C2-dA-2,3-Dihydroxy-5,7,9(10)-estratriene-4,17-dione
KPO4 buffer pH 7.4, 37 °C for 7 h or Calf-thymus DNA 1-N3,3-(N4-dC)-2,3-Dihydroxy-5,7,9(10)-estratriene-4,17-dione.
4-OHEN 4-OHEN or 4-OHEN-diacetate + MCF7 cells 1-N6,3-C2-dA-2,3-Dihydroxy-5,7,9(10)-estratriene-4,17-dione SID-LC-MS/MS Wang76
N3,3-(N4-dC)-2,3-Dihydroxy-5,7,9(10)-estratriene-4,17-dione.
4-OHEN 4-OHEN + SD rat mammary gland injection 2-N1,3-(N2-dG)-1,3-Dihydroxy-5,7,9(10)-estratriene-4,17-dione LC-MS/MS Zhang et al.40
1-N6,3-C2-dA-2,3-Dihydroxy-5,7,9(10)-estratriene-4,17-dione
NQ dG/dA acetic acid/water/DMF 1,2-Dihydroxy-naphthalene-4-N7-gaunine UPLC/MS Saeed et al.69
dG/acetic acid : water 1,2-Dihydroxy-naphthalene-4-N3-adenine UPLC/MS Saeed et al69
Naphthalene-1,2-dion-4-yl-N7-guanine NMR/MS McCoull et al.70
PQ dG/acetic acid : water or Calf Thymus DNA Phenanthrene-1,2-dion-4-yl-N7-guanine NMR/MS McCoull et al.70
BPQ dG /acetic acid : water Benzo[a]pyrene-7,8-dion-10-yl-N7-guanine NMR/MS McCoull et al.70
BPQ dG or dA/DMF/55 °C/pH 7.0 10-(N2-dG)-9,10-dihydro-9-hydroxy-B[a]P-7,8-dione NMR Balu et al.19
8-N1,9-(N2-dG)-8,10-Dihydroxy-9,10-dihydro-B[a]P-7(8H)-one
8-N6,10-N1-dA-8,9-Dihydroxy-9,10-dihydro-B[a]P-7(8H)-one
BPQ A549 cells and HBEC-tk cells incubated with 2 μM B [a]P-7,8-dione in HBSS + pyruvate 6-(N2-dG)-9,10-Dihydro-10-hydroxy-B[a]P-7,8-dione LC-MS/MS Huang et al.44
10-(N1-dG)-9,10-Dihydro-9-hydroxy-B[a]P-7,8-dione LC-MS/MS Huang et al.44
10-(N6-dGA)-9,10-Dihydro-9-hydroxy-B[a]P-7,8-dione LC-MS/MS Huang et al.44
10-(N3-dA)-9,10-Dihydro-9-hydroxy-B[a]P-7,8-dione LC-MS/MS Huang et al.44
10-(N3-dA)-B[a]P-7,8-dione LC-MS/MS Huang et al.44